8 Songs About (Ahem …) the ‘First Time’

Kenny Chesney famously sings, "The first time's a one-time feeling and I never wanted nothing more," while Sara Evans expresses deep remorse during her song about the loss of innocence.

A performance of Conway Twitty singing "You've Never Been This Far Before" is at best uncomfortable decades later. Why does the famous country romantic have to stare at the camera like that?

An unreleased Kip Moore song called "Backseat" recalls the sheer awkwardness of young lovers going all the way for the very first time. Deana Carter's "Strawberry Wine" may best summarize the complexity of one's first sexual encounter. It's a toxic mix of euphoria, confusion, guilt and burning desire that you don't really get to unpack until many years later. We romanticize the memory, but often the first time is the worst time.

Country songs about sex aren't rare, but lyrics that go a step further to paint a picture of first-time love are precious. "That Summer" by Garth Brooks is a memorable example not included in our video (no suitable versions are allowed on YouTube). Here the narrator loses his virginity to an older woman — a singular pretense for a '90s country song to be sure, but once you hear the song you realize it's neither provocative nor obscene.

Normally we ask you to share a story of a song you relate to, but in this case, we'll just ask for you to name a favorite on this list of first-time songs. It's possible we missed one or two — please correct us! After you finish, subscribe and watch more This List videos, like this one that shows 10 country songs that you think were hits that weren't.